INTRODUCTION
All my life I have been addicted to anal sex. My infatuation with girl's and women's shapely bottoms began even before I was of legal age to have sex. I was always attracted to girls with shapely legs and curvy bottoms. I was not that attracted to girls with big tits like so many men. I was always a leg and ass man. As much as I loved shapely bottoms I didn't have anal sex until I was 18 years old when I was in high school. Once the wick was dipped however, I was hooked. There was nothing I liked more than having a girl or woman on all fours with my cock sliding in and out of her curvy ass.
I found that some girls liked anal sex and in fact some actually preferred it to vaginal or oral sex. Others willingly gave up their ass in order to have their pussies taken good care of and of course there were those who would never give up their ass. The next best thing for me was fucking a pussy doggy style if the girl had a hot ass but anal was the ultimate surrender. My infatuation started in junior high school where I was always checking out girl's bottoms. It was the mid 1950's and girls wore long tight skirts to school. I always tried to imagine what those shapely buns looked like naked. The closest I would ever come to seeing them naked was at the community swimming pool.
My infatuation continued all through high school until I graduated in 1959. I only had sex with one girl in high school when we were both 18 years old. I began dating Jean Riggio a cute little Italian girl in my senior year. I played varsity sports and Jean was a cheerleader. She was only about 5'3" and weighed under100 pounds. She had short reddish brown hair with shapely legs and a killer ass. Jean was flat chested and most of the guys were going for the girls with big tits back then. Jean was thrilled that I had asked her to go steady.
DATING JEAN
Jean was a virgin when she and I started dating but I was determined to seduce her and I eventually convinced Jean to expand her horizons. It started out with heavy make-out sessions and petting, which always left Jean's panties soaking wet and my car filled with the smell of sex. Jean's flat tits would be exposed and I would suck and roll the nipples between my fingers until they were eraser hard. Jean would have orgasms just from me playing with her tiny tits. Later in our dating I would stroke Jean's thighs when I sucked her tits, occasionally brushing my hand against her panty covered pussy. Jean would jump and moan each time my hand came in contact with her cunt.
One night after one of my ball games, I drove Jean to our favorite make out spot. Jean was still dressed in her cheerleading outfit and before long her sweater and sport bra was pushed up over her flat tits. I sucked her tits and stroked her thighs. This time I moved my hand inside her panties and stroked her clit. Jean went wild and humped my hand. I then eased her panties down and off her legs. Next I moved between her legs and positioned them over my shoulders. Jean was shaking in anticipation as I began to lick her pussy and cup her beautiful ass cheeks. Jean came numerous times humping her pussy against my face and soaking me with her cum.
I moved up along side Jean and kissed her deeply allowing her to taste her own pussy juice. She asked what she could do to reciprocate so I steered her petite hands to my exposed engorged cock. Jean stared at it in awe not knowing what she was supposed to do next. I guided her through hand job techniques and soon had Jean licking and kissing my cock. I moved her to the next level of sucking the head of my big cock and fondling my semen filled balls. Jean started to get into it and tried to take more and more of my cock in her mouth. I could feel my orgasm building but elected not to warn Jean.
My first burst of cum caught her totally by surprise and when she felt the second burst she tried to swallow the first. Her mouth quickly filled with cum and to prevent gagging she pulled my cock from her mouth. My cock kept firing cum and it hit her in the face, hair and bare tits. Jean giggled as she held my spurting cock in her hands as cum flew everywhere. Jean had come along way since our first date.
The next several dates were repeat performances and Jean had become comfortable with both of us being totally naked. I added variations to our sex. I taught her about sixty-nine so we could eat each other together. I also introduced my finger into her asshole as I ate her pussy. I placed Jean on all fours, licked her pussy and rimmed her asshole. One night I placed just the head of my cock in her pussy and rubbed her clit with the soft head of my cock. Jean went wild and had multiple orgasms.
Jean told me that she was ready to fuck but she didn't want to do it in the car. She planned to do it at her house when her parents were away. One Saturday her parents were invited to a wedding and they would be gone the whole day. Her parents had no sooner pulled out of the driveway that I was over at the house. We went straight to Jean's room and took off all of our clothes.
With Jean lying back on her bed, I slid between her legs and I was gentle and patient as I eased my throbbing cock into her pussy. The pressure of my fullness almost negated the pain of losing her virginity. The pain soon subsided and Jean only felt pleasure as my large cock touched every fiber of her cunt. I fucked her slowly with long deep strokes and Jean began to hump her cunt up at me. She had numerous orgasms with the last ones violent and vocal. I tensed and flooded her pussy to overflowing with cum. I continued to pump her pussy and she could feel the juices running out of her cunt and trickling down her thighs. Jean held me tightly as she felt she was in heaven.
The rest of the day we showered, had more sex and stayed naked all day. At one point we took a bath together in her parent's big tub. After the bath I gave Jean a massage with her mother's body lotion. First I massaged the front of her body paying special attention to her nipples and her pussy. Sensing that she was on the verge of another orgasm I slipped my cock into her cunt and humped Jean wildly.
I then rolled Jean over on her stomach and massaged her back, shoulders and the back of legs. I kneaded her gorgeous ass cheeks and as I massaged her ass I put an ample amount of lotion on her asshole. Then I began to probe her asshole first with one and then two fingers. Before long my fingers were moving easily in and out of Jean's thoroughly lubed asshole. I lifted Jean up by her hips until her ass was in the air as she rested her head on the mattress. She looked beautiful with her shapely ass in the air and I knew that I just had to have it. I removed my fingers and positioned the head of my cock at the entrance to her ass. As I eased my cock into her bunghole I heard Jean gasp and hold her breath. I told her to relax and I promised that I would not injure her.
As I eased my cock into her ass the head cleared her sphincter as Jean uttered an audible gasp. I continued to ease my cock in and out of her asshole feeding her an additional ¼ to ½ inch at a time, each time waiting until she relaxed. It seemed to take hours before my entire 8+" were lodged deep in her ass. If I had not cum so many times already I would have shot my wad quickly. I started to fuck her with long deliberate strokes as I admired her beautiful ass accepting my huge cock. I stroked her marvelous ass cheeks and told her how good she looked in this position with my dick in her luscious ass.
I felt my orgasm start down in my balls and rush up through my cock flooding Jean's rectum. I ejaculated more than I expected and cum soon filled her asshole to overflowing and then backed up coating my cock and running down the inside of her thighs. We both collapsed on her bed and rolled to our sides with my cock still imbedded in Jean's ass. My cock eventually softened and slipped from her asshole with an audile pop.
Jean and I continued our sexual escapades on a regular basis. Jean could always count on having all three of her holes filled with cum on each occasion. Then there was that fateful day when we got caught. Her parents had left for the day and as usual Jean and I were naked in bed within minutes. On this particular day I was anxious to fuck Jean's hot curvy ass so as soon as I had eaten her pussy I placed her on all fours. I was pounding her ass with my big hard cock when I looked up and saw both her parents standing in the doorway with their mouths agape. I was on the verge of a massive cum shot, so when I pulled out, my cock spewed cum all over Jean's naked body.
I just knelt there as cum shot out of my cock and landed on Jean's short hair, neck, shoulders, back and buttocks. Her parents were speechless as they watched my big cock unleash its fury. I noticed that Jean's mother stared at my large pulsating cock almost with interest. Then Jean's father screamed for me to get out of the house and never return. That's when Jean realized that we were busted. I scrambled out of the bed, scooped up my clothes and ran down the stairs to the first level. I dressed as fast as I could as Jean's parents yelled at Jean in her bedroom.
I made a dash for my car and drove home. I was sure that Jean's parents would call mine but they never did. Days later Jean's father met with me and told me that he expected me to keep my mouth shut about having sex with his daughter. He also told me that I was never to date Jean again. I didn't know what to say so I just nodded in agreement. What do you say when a girl's parents catch you with your cock in their daughter's ass?
A MEETING WITH JEAN'S MOTHER ANN
I didn't date jean for the rest of the year even though we were both tempted to still see each other secretly. Jean's father had threatened her with boarding school if he ever suspected that she was having sex again. I dated some other girls the rest of the school year but I never had sex with any of them other than hand jobs and pussy licking.
That summer I was working at the local grocery store before I headed off to boot camp. Most of my friends were going to college but I had enlisted in the Marines. One day Jean's mother came into the store and purchased a large order of groceries. She asked the manger if I could deliver them to her home. The manager agreed and told me to deliver the groceries to the Riggio's home. I was nervous as I felt that Jean's mom had purposely requested me to deliver her groceries. I was worried that she may have finally got up the nerve to confront me about the day she caught me with Jean. My thoughts could not have been more unfounded.
I pulled into the driveway of the house and walked around to the back door that led into the kitchen. I knocked on the door and waited for Mrs. Riggio to answer. I was shocked when she opened the door and she was totally naked. My mouth fell open as I stared at Jean's naked mother.
"Oh you got here quickly. Please bring the groceries in and set them on the kitchen counter," she said and then closed the door part way.
I assumed that she wasn't expecting me so soon but I was still confused as to why she was naked when she opened the door. Mrs. Riggio had short blonde hair and I now I knew that she was indeed a natural blonde. She was about 5'6" tall and couldn't have weighed more than 120 lbs. Her breasts I guessed to be a 33 -34 B cup and they turned up slightly with her nipples pointing up in the air. Later I would learn that they really pointed up when she was excited. She had a narrow waist, very pretty legs and a nice round bottom. Her figure was near perfect in proportion. It was obvious where Jean got her good looks and curvy ass.
I stepped inside the house with the last bag of groceries and put them on the counter and I could feel my cock harden in my pants. Mrs. Riggio offered me a cup of coffee and told me to sit at the kitchen table. She poured me a cup of coffee and brought it over to me. Then she returned to the kitchen counter and finished putting the groceries away. I stared at her shapely legs and marvelous ass as she went about her business as if I wasn't even there. The more I stared at her ass the harder my cock got. Then I thought about Mr. Riggio and Jean.
"I better get going Mrs. Riggio," I stammered.
"Relax, enjoy your coffee," she said persuasively.
"But what about your husband and Jean?" I asked nervously.
"Don't worry about them they are visiting a college campus and they won't be back until tomorrow," she assured me.
"I know that you are a leg and ass man. Do you like my legs and ass?" she asked me directly.
"You have a beautiful ass and very lovely legs, Mrs. Riggio. I think that your figure is fabulous," I replied nervously but honestly.
"Thank you! I'm almost finished here and please call me Ann," she said.
I sipped my coffee until Ann finished at the sink and then she told me to follow her. I walked behind her up the stairs watching her ass sway and by the time we reached the bedroom my cock was straining in my pants. Ann went in the room and turned the bed covers down and then she got in the bed on her back.
"I want you to eat me first then fuck me and if you do a good job I will let you have my ass," Ann whispered sexily.
I stood frozen to the spot. Here was Jean's mother telling me to eat her and fuck her and promising to give me her hot ass. I didn't know what to do so I didn't move for a second. Then she patted her pussy in an invitation and I was out of my clothes in record time and between Ann's legs. I dove right into her pussy and licked away at her tasty twat. Ann was a little surprised at my aggressiveness but she loved the technique and she soon had her first orgasm.
"Oh boy, this is a quick one. Oh eat me yes that's it right there," she cried out.
Ann's body trembled in orgasm as I continued to eat her pussy. I was determined to make her cum several times before I fucked her. After several mild orgasms, Ann's body lifted off the bed with the intensity of her biggest climax. Her mouth opened as if to scream but no sounds came out and her body gyrated out of control. I held tightly to her legs and tried to keep my mouth fastened to her cunt but her body moved too violently. Her entire body went stiff and then she screamed aloud just as she came hard. Then she collapsed like deflated balloon and lay flat on the bed. I did not give her a chance to recover as I slid my throbbing cock into her pussy. She gasped when I entered her and then I began to fuck her slowly.
I was so turned on that I came shortly after my cock entered her pussy. Cum flew from my cock deep into her pussy as I flooded her womb to overflowing. I managed to stay hard so I kept right on fucking her and I could feel my cock swimming around in the combined juices in her pussy. Ann started to build toward another orgasm and I picked up the pace in hopes that we could cum together. Soon we were pounding at each other's body and it seemed more like wresting than fucking. It almost became a contest to see who could cum first or who could last the longest and I wasn't really sure of either.
Ann stiffened under me momentarily and then her body thrust up and around as if she was trying to buck me off of her. I fought back and drilled my cock into her. She was gasping as if she was trying to breathe but I knew that she was having a massive orgasm. Just at the height of her climax I unleashed my load into her for a second time. The two of us thrashed about and locked onto each other as the intense orgasms overtook our bodies. We both then collapsed on the bed with me on top of her. After we calmed I rolled over on my back next to Ann and we both lay on her backs side by side.
Ann spoke first, "That was incredible! I suspected that you are a good lover."
"So did I do well enough to get your ass?" I asked with confidence this time.
"By all means I'm sure that you have something left for that today?"
"Just give me a few minutes and once I look at your gorgeous ass again I'll be ready."
"Have you ever rimmed anyone? Would do that for me too? I douched my pussy and ass in hopes that we would make it together"
"Of course I would love to eat your luscious ass."
"Ohhh!" was all Ann could say.
We played with each other for quite awhile with Ann stroking my cock and me rubbing her tits and ass. I then rolled Ann over on all fours, lifted her gorgeous ass in the air and slipped my tongue in the crack of her ass. Ann gasped aloud when my tongue touched her nether hole and the she moaned and groaned as I continued to rim her asshole. She was going wild and she had shoved her hand back in her pussy as I plunged my tongue deeper and deeper into her anus. Finally I knelt behind her and lined up my cock with her asshole.
"Wait, oh wait, get some cream on your cock," Ann cried out.
She frantically got some lotion from her nightstand and handed it to me. I put an ample amount of lube on my cock and in her asshole. I stroked my cock as I fingered her ass and I took my time as I loved fingering her shapely bottom. Ann cooed as I fingered her and then she got impatient.
"Stop teasing me and get your big cock in there," she yelled.
I smiled as I had the desired effect on her. I eased my cock into her snug ass in one steady slow movement until I was all the way in. Ann seemed to hold her breath during the penetration but once I started moving she got into it. She thrust her ass back at me just as I thrust forward into her ass. We got a good rhythm going and soon we were fucking in unison as if we had done this many times before.
"Oh God this is great. Fuck my ass drill me shove it in deep," Ann screamed.
She was gasping and grunting as I really began to pummel her ass. When I reached for her pussy I found her hand already in place frigging herself frantically. I picked up the pace and held to Ann's shapely buttocks as our hips slapped noisily together. She was really into it now and the two of us fucked like animals.
"Oh yeah that's it, that's the way to fuck my ass. Give it to me, cum in me, cum in my ass," she screamed.
We were both grunting from the physical intensity of our butt fucking. I slammed into her as my cock now moved in her tight ass. I felt my orgasm approaching and as much as I wanted to prolong the ass fucking session, I couldn't. My body stiffened and I plunged my cock all the way into her gorgeous ass. Streams of semen shot into her rectum as I seemed to cum continuously for several minutes.
"Oh good, I feel it," she cried out and then her own orgasm hit her, "Oh my, I'm cumming again!"
Her body thrashed around as I held onto her curvy ass cheeks and kept my cock buried in her ass. Her body danced around and it was all I could do to keep my cock in her ass. She then collapsed face down on the bed and my cock slipped from her ass with an audible pop. I ran my cock over her buttocks rubbing the remaining cum on her curvy ass. She wiggled her bottom and squealed in delight. She was surprised with the amount of cum that I generated for my third orgasm of the afternoon. We both lay on her bed totally drained for several minutes without talking and then Ann broke our silence.
"I need a shower want to join me," she asked.
"Sure," I replied.
The two of us showered and washed each other. On another day it would be fun to fuck in the shower but Ann was definitely fucked out. After the shower we dried off and got dressed and I headed back to my place. For the next three weeks before I headed to Parris Island for boot camp, Ann and I fucked a couple of more times when Jean and Mr. Riggio were checking out campuses. I also learned that Ann was banging the gardener and that she loved it in the ass, something her husband wouldn't do for her. The time I spent with Ann furthered my resolve and desire for anal sex.